Wireless devices, such smartphones, tablets, and the like, have become an increasingly common and integral part of everyday life. Indeed, wireless devices are used to send text, emails, and network socially, pay bills, take pictures, monitor health, track diet, listen to music, watch movies, browse, online shopping, and a variety of operations. Concurrent with the rise of wireless devices is the rise of security risks associated with their use. For example, sending private confidential email over an unencrypted or weakly encrypted wireless link may make the device vulnerable to attacks, such as eavesdropping and the like. However, the complexity of wireless devices and the security technologies used make it difficult for a user to detect and understand the impact of such vulnerabilities. Due to scientific advances and increasing computational power, security technologies that were secure to use a few years ago have become unsecure. This increases the complexity for a user to evaluate his or her own data risk.